Optically active pyridonecarboxylic acid derivatives

1. A stereoisomerically pure N 1 -(1,2-cis-2-halogenocyclopropyl)-substituted pyridonecarboxylic acid derivative represented by the following formula (I):

wherein R 1 represents a hydrogen atom, an amino group, a hydroxyl group or a thiol group;

R 2 represents a substituent represented by the following formula:

 wherein R 23 and R 24 together are (CH 2 )j; where j=2 to 5;

A represents C—X 3 or a nitrogen atom;

X 1 and X 2 , which may be the same or different, each represents a halogen atom;

and X 3 represents a halogen atom, an alkyl group of from 1 to 6 carbon atoms, an alkoxyl group from 1 to 6 carbon atoms, a cyano group, a trifluoromethyl group, or a hydrogen atom;

or a pharmaceutically acceptable salt thereof.

2. 7-[7-(S)-Amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[2-(S)-2-fluoro-1-(R)-cyclopropyl) ]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid or a pharmaceutically acceptable salt thereof.

3. A method for treating bacterial infections which comprises administering a therapeutically effective amount of 7-[7-(S)-Amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[2-(S)-2-fluoro-1-(R)-cyclopropyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid or a pharmaceutically acceptable salt thereof.

4. 7-[7-(S)-Amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-(1,2-cis-2-fluorocyclopropyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid or a pharmaceutically acceptable salt thereof.

5. An antibacterial composition comprising a therapeutically effective amount of, as an active ingredient, 7-[7-(S)-Amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[2-(S)-2-fluoro-1-(R)-cyclopropyl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.

6. The stereoisometrically stereoisomerically pure N 1 -(1,2-cis-2-halogenocyclopropyl)-substituted pyridonecarboxylic acid derivative of claim 1 , wherein R 2 represents a 7-amino-5-azaspiro[2,4]-heptan-5-yl group.

7. The stereoisomerically pure N 1 -(1,2-cis-2-halogenocyclopropyl)-substituted pyridonecarboxylic acid derivative of claim 6 , wherein R 2 represents a 7-(S)-amino-5-azaspiro [2,4 2 . 4 ]heptan-5-yl group.

8. The stereoisomerically pure N 1 -(1,2-cis-2-halogenocyclopropyl)-substituted pyridonecarboxylic acid derivative or a pharmaceutically acceptable salt thereof of claim 1 , wherein R 2 represents 8-amino-6-azaspiro[3,4 3 . 4 ]octan-6-yl group.

9. A method for treating bacterial infections which comprises administering a therapeutically effective amount of the stereoisomerically pure N 1 -(1,2-cis-2-halogenocyclopropyl)-substituted pyridonecarboxylic acid derivative or a pharmaceutically acceptable salt thereof of claim 1 , wherein R 2 represents 8-amino-6-azaspiro[3,4 3 . 4 ]octan-6-yl group.

10. Stereoisomerically pure 7 -[( 7 S )- 7 - amino - 5 - azaspiro[ 2 . 4 ]heptan - 5 - yl] - 6 - fluoro - 1 -[( 1 R, 2 S )- 2 - fluoro - 1 - cyclopropyl] - 8 - methoxy - 1 , 4 - dihydro - 4 - oxo - 3 - quinolinecarboxylic acid or a pharmaceutically acceptable salt thereof.

11. A method for treating bacterial infections which comprises administering a therapeutically effective amount of stereoisomerically pure 7 -[( 7 S )- 7 - amino - 5 - azaspiro[ 2 . 4 ]heptan - 5 - yl] - 6 - fluoro - 1 -[( 1 R, 2 S )- 2 - fluoro - 1 - cyclopropyl] - 8 - methoxy - 1 , 4 - dihydro - 4 - oxo - 3 - quinolinecarboxylic acid or a pharmaceutically acceptable salt thereof.

12. An antibacterial composition comprising a therapeutically effective amount of, as an active ingredient, stereoisomerically pure 7 -[( 7 S )- 7 - amino - 5 - azaspiro[ 2 . 4 ]heptan - 5 - yl] - 6 - fluoro - 1 -[( 1 R, 2 S )- 2 - fluoro - 1 - cyclopropyl] - 8 - methoxy - 1 , 4 - dihydro - 4 - oxo - 3 - quinolinecarboxylic acid or a pharmaceutically acceptable salt thereof, in combination with a pharmaceutically acceptable carrier.